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On-Demand Continuous Flow Synthesis of Pentafluorosulfanyl Chloride (SF5Cl) Using a Custom-Made Stirring Packed-Bed
Lauriane C Peyrical1, Thibaud Mabit1, Vanessa Kairouz1
1Université de Montréal, FRQNT Centre in Green Chemistry and Catalysis, Centre for Continuous Flow Synthesis, Department of Chemistry, 1375 av. Thérèse Lavoie-Roux, Montréal, QC, H2V 0B3, Canada.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 15, 2025
Summary
This study presents the first continuous flow synthesis of pentafluorosulfanyl chloride (SF5Cl), a key reagent for creating SF5-substituted compounds. This new method offers a practical and efficient way to produce SF5Cl using simple starting materials.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Fluorine Chemistry
Background:
- The pentafluorosulfanyl (SF5) group is of growing interest in medicinal chemistry and materials science.
- Current synthetic methods for SF5-containing compounds are often impractical due to challenges in reagent synthesis and installation.
- Pentafluorosulfanyl chloride (SF5Cl) is a crucial reagent for introducing the SF5 group, but its synthesis has been limited.
Purpose of the Study:
- To develop the first continuous flow synthesis of pentafluorosulfanyl chloride (SF5Cl).
- To establish a safe, efficient, and on-demand method for SF5Cl production.
- To demonstrate the utility of the synthesized SF5Cl in subsequent chemical transformations.
Main Methods:
- Utilized inexpensive and readily available reagents: sulfur powder (S8), trichloroisocyanuric acid (TCCA), and potassium fluoride (KF).
- Designed and employed a custom stirring reactor for continuous flow synthesis.
- Performed radical addition reactions of SF5Cl onto alkynes in a telescoped process.
Main Results:
- Achieved the first continuous flow synthesis of SF5Cl.
- Demonstrated a safe, fast, and highly efficient on-demand production of SF5Cl.
- Successfully applied the generated SF5Cl in a telescoped radical addition reaction with alkynes.
Conclusions:
- The developed continuous flow method provides a practical solution for the synthesis of SF5Cl.
- This approach overcomes previous limitations in the accessibility and handling of SF5Cl.
- The on-demand synthesis and application of SF5Cl in flow chemistry opens new avenues for SF5-substituted compound preparation.
